Wallflower (Erysimum Cheiri (L.) Crantz) from Past to Future

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Research Journal of Pharmacognosy (RJP) 6(2), 2019: 85-95 Received: 23 June 2018 Accepted: 4 Nov 2018 Published online: 10 Mar 2019 DOI: 10.22127/rjp.2019.84330 Review article

Wallflower (Erysimum cheiri (L.) Crantz) from Past to Future

Ghazaleh Mosleh1 , Parmis Badr2,3, Amir Azadi3,4, Zohreh Abolhassanzadeh3, Seyed Vahid Hosseini5, Abdolali Mohagheghzadeh1,3*

1Department of Phytopharmaceuticals (Traditional Pharmacy), Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran. 2Phytopharmaceutical Technology and Traditional Medicine Incubator, Shiraz University of Medical Sciences, Shiraz, Iran. 3Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran. 4Department of Pharmaceutics, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran. 5Shahid Faghihi Clinic, Colo-rectal Research Center, Shiraz University of Medical Sciences, Shiraz, Iran.

Abstract Wallflower (Erysimum cheiri (L.) Crantz) is a common medicinal plant in Persian medicine and nowadays some traditional products from wallflower are consumed on global markets. The aim of the present study was to study the phytochemical constituents of wallflower and discuss safety evaluations related to the traditional wallflower preparations. Major Persian scholars (e.g. Avicenna) books, Persian manuscripts (e.g. Makhzan-al-advia) and Arabic medical manuscripts (e.g Alshamel-fi alsanaat altebya) of the medieval Islamic era as well as current search engines including Pubmed, Scopus, Siencedirect, and Google Scholar were included in the study from 1700 up to 2018 A.D. In traditional medicine manuscripts, various topical and oral dosage forms of wallflower were administered in low doses. After renaissance, phytochemical investigations reported cardiac steroids in wallflower and it might be the reason that next medical investigations on the herb have been interrupted. According to in vivo studies, topical indications of cardiac steroids in doses lower than their inhibitory concentration 50 (IC50) should be safe and effective in some cutaneous disorders. Wallflower is reported to have several different classes of compounds including: 11 types of cardenolides (such as strophanthidin, bipindogenin, uzarigenin, cannogenol and digitoxygenin derivatives), two flavonoids, a cyanidin and two glucosinolates. Therefore, for safety guarantee, wallflower products require dose adjustment based on IC50 and probable cardenolide soluble content in that dosage forms.

Keywords: Erysimum cheiri; phytochemistry; wallflower Citation: Mosleh G, Badr P, Azadi A, Abolhassanzadeh Z, Hosseini SV, Mohagheghzadeh A. Wallflower (Erysimum cheiri (L.) Crantz) from past to future. Res J Pharmacogn. 2019; 6(2): 85-95.

Introduction Wallflower (Erysimum cheiri (L.) Crantz), perennial herb that grows up to 25-80 cm (figure synonyms: Cheiranthus cheiri L. from 1). Botanically, the leaves are lanceolate shaped Brassicaceae family [1], is a common medicinal and are 5-10 cm in long, the flowers have four plant in Persian medicine (PM) while, it is not sepals and six stamens [3] have a pleasant popular in modern medicine. Wallflower is an fragrance and are arranged in dense racemes. The ornamental herb which is native to Europe, color of flowers is golden yellow to orange especially Mediterranean region and is yellow. The fruit is a silique which has distinct extensively cultivated around the world [2]. It is a ribs and the seeds are arranged in one row [4].

*Corresponding author: [email protected] © 2018. Open access. This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by-nc/4.0/) Mosleh G. et al.

The inner surface of the fruit has trichomes and wallflower and goldlack (German common on its valves are usually 4-5-rayed, few 3-rayed, name), from 1700 up to 2018 A.D. History of and infrequently 6-7-rayed [5]. Seeds are sub- phytochemical investigations on wallflower was orbicular, pale brown and about 3 mm long [3]. provided and summarized in a diagram according Wallflower description in the traditional medical to available articles [13-27]. Drawing of the manuscripts is in agreement with the above molecular structures was done by ChemDraw Pro botanical description [6-12]. Some traditional 8.0 software. preparations are available in global herbal markets containing wallflower as an ingredient. Results and Discussion Because of cardiotonic constituents of wallflower Wallflower from past to present organs, toxicity and safety of corresponding A brief history of wallflower investigations has products should be mentioned in detail [13-27]. been demonstrated in figure 2. Wallflower was This study has been conducted to provide well known as a medicinal plant in Persian and information on phytochemistry, traditional and Arabic medical manuscripts of the medieval current medicinal properties of wallflower Islamic era [6-12]. Later, a large number of preparations and it emphasizes the necessity of studies have been directed on phytochemical safety considerations for wallflower products. studies of wallflower [13-27]. In 1899, an isolated cardiac glycoside (cheiranthin) was introduced as a new remedy extracted from wallflower [17]. In 1932, in vivo toxicological studies on cheiranthin made some safety concerns [22]. Cheiranthin and cheirinine were reported as wallflower chemical compounds in the early phytochemical investigations [14]; however, they has not been identified as pure chemical compounds by current phytochemistry In 1994, a review on wallflower cardiac glycosides [25]. And in 2001, a pharmacological in vivo study on wallflower were published. It introduced wallflower as a medicinal plant which was used clinically in some skin diseases [26]. Based on Persian and Arabic medical manuscripts of the medieval Islamic era, various wallflower dosage forms have different medicinal effects. Wallflower had oral, topical and vaginal but no parenteral indications in Persian medicine. Topical dilute decoction of the flower was recognized as a good remedy for aphthous and inflammations. Topical oil of flower has been Figure 1. Wallflower (Erysimum cheiri (L.) Crantz) reported as analgesic, anti-inflammation and hair (photographed by authors) tonic. Cerate dosage form is suggested as anti- fissure (both anal and skin fissure) and wound Methods healer. Root in a topical decoction or poultice has PM literature including, “Al hawi”, the Canon of been reported as analgesic and anti-inflammatory medicine, “Tohfeh al- momenin”, “Makhzan-al- agent. The seeds in the form of sitz bath or advia” and “Mohit-e azam” as well as medicinal vaginal suppository have been administered as manuscript from Arabian scholars i.e.: emmenagogue, abortifacient and labor inducer “Alshamel-fi alsanaat altebya”, “Hadiqat ol- [6-12]. Nowadays, wallflower preparations are azhar” were searched with terms of cheir-e zard available in herbal markets for traditional and cheir-e asfar [6-12]. Main part of this study medicine requests. In Iran, there is a traditional was performed via electronic search on Pubmed, medicine ointment compound from E. cheiri and Scopus, Siencedirect, and GoogleScholar with Helianthus annuus which is used for anal fissure terms of Cheiri, Erysimum, Cheiranthus, treatment [28]. In Indian markets there is a multi- 86 Res J Pharmacogn 6(2): 85-95 Erysimum cheiri component tablet containing wallflower for breastfeeding mothers to improve lactation [29].

Figure 2. A brief history of wallflower investigations

In traditional societies of present India, and multi-component preparations. Infusion is wallflower is still used as an abortifacient agent permitted in the form of mixing 2-3 g dried [30]. In Indian medicine, flowers are flower in 100 mL water (3-4 cups daily) [4]. recommended as cardioactive, antispasmodic, Although oral administration of wallflower is purgative, emmenagogue, deobstruent and tonic. considered to have low resorption rate Besides, wallflower seeds are known as (absorption into the circulation of cells or tissue), stomachic, diuretic, expectorant, but goitrogenic, its parenteral dosage form is considered to have and the extracts of leaves and the seeds are strong efficacy and probably poisoning effects antibacterial [31]. Wallflower is used as [4]. According to European Food Safety cardioactive, emmenoguge, fertilizer and anti- Authority (EFSA) cheirotoxin (cardiotonic and paralysis agent in Pakistan [32]. The leaves and antineoplastic agent) is a chemical of concern flowers are listed in herbal ingredients of “Asian [13,35]. In addition to cheirotoxin, cheirosid A medicines”, which are used in west as fertilizer and glucocheirolin are categorized as moderately agent, anti-paralysis, emmenagogue, cardiotonic hazardous compounds [35,43] and wallflower is and expectorant [33]. In German phytotherapy, identified to have cytotoxic action [44]. Hazard the dried flowers as well as the seeds and roots and toxicity of cheiroside A is described by lethal are considered to be anti-itching, emmenoguge, dose of 0.681 mg/kg in cats by intravenous fertilizer and anti-tumor [34]. administration, and lethal dose of cheiroline is reported as 3-7 mg/kg in Mus (a subgenus of the Phytochemistry of wallflower rodent genus) by intravenous administration [13]. According to literature, different parts of the herb There is a suspect for goitrogenic properties of have special profiles of compounds. Table 1 has cheiroline [45]. In vitro, cheiroline increases explained chemical composition of wallflower activation and expression of Nrf2 as well as organs in details. Molecular structures of expression of hemeoxygenase 1 and γ- wallflower chemical compounds have been glutamylcysteine. In addition, cheiroline is an presented in figure 1. antibacterial and antifungal agent. Also in vitro anti-bacterial effects of cheiroline on H. pylori Wallflower pharmacology and toxicology has been proved [13,46,47]. The minimum lethal Despite the safety concerns, there is no report of dose of cheiranthin for the frog has been reported health hazard or side effects about oral to be 2.2×l0-7 g/g [22]. Cheiranthin showed the administration of wallflower [4,42]. Dried characteristics of systolic rest in frogs [48]. flowers, dried ripe seeds and fresh aerial parts of Wallflower root intravenously applied in the plant before flowering, are reported to have anaesthetized rabbits has resulted in obvious medicinal properties as internal drops, infusion 87 Mosleh G. et al. vasodilation and bradycardia that eventually led (33) Oleic acid (C18H34O2) Seed [39] to the animal's death [49].

Table 1. Natural components from wallflower Toxicity concerns of cardiac glycosides are due Compounds and molecular Plant + + No. References to inhibition of Na K ATPase mechanism. formula part(s) Terpenoides There are various factors affecting the amount of - Cardenolides cardenolide absorption in transdermal indications. Seed, (1) Cheirotoxin (C H O ) [4,35] Area and nature of wound are two important 35 52 15 Aerial parts (2) Deglucocheirotoxin (C29H42O10) Seed [25] parameters responsible for cardenolide toxicity. (3) Erysimoside (C35H52O14) Seed [4,25] Also cutaneous circulation, frequency, duration (4) Glucoerysimoside (C41 H62O19) Seed [4] and formulation characteristics are other (5) Alliside (C29H44O10) Seed [25] (6) Glucoalliside (C36H56O15) Seed [25] parameters affecting absorption of cardenolides Glucobipindogulomethyloside (7) Seed [25] [50]. On the other hand, application of (C35H54O15) (8) Cheiroside A (C35H54O13) Seed [4] cardenolide containing herbs in dermal dosage (9) Neouzarin (C35H54O14) Seed [25,36] forms has a profound history [8,51]. Topical (10) Erycordin (C35H54O14) Seed [25] application of cardenolides in the safe doses (11) Digifucocellobioside (C41H64O18) Seed [25] -Monoterpenoids lower than their inhibitory concentration 50% Essential Geraniol: 3,7-Dimethyl-2,6- (IC ) could accelerate dermal collagen synthesis (12) oil of [37] 50 octadien-1-ol (C H O) (E) form 10 18 flower [52]. An in vivo study on wallflower has shown Essential Nerol: 3,7-Dimethyl-2,6- anti-tumor properties of topical wallflower (13) oil of [37] octadien-1-ol (C H O) (Z) form 10 18 flower extract on murine skin. It has introduced Essential wallflower as a medicinal plant, used clinically in (14) Linalool (C10H18O) oil of [37] flower some skin diseases like inflammations [26]. Phenylpropanoids -Flavonoids Conclusion (15) Isorhamnetin (C16H12O7) Herb [13] Isorhamnetin 3,7-diglycosides In Persian and Arabic medical manuscripts of the (16) Herb [13] (C27H30O15) medieval Islamic era, various topical dosage (17) Kaempferol (C15H10O6) Flower [31] -Cyanidins forms of wallflower (in low doses) have been Cyanidin 3,5-diglycosides recommended for wound healing, analgesic and (18) +1 Flower [27,38] (C41H45O22 ) anti-inflammatory purposes. Although parenteral - Others Essential rout of administration was not suggested in (19) Anis aldehyde (C8H8O2) oil of [37] traditional medicine, oral or vaginal dosage forms flower Essential mostly have been indicated for emmenoguge, (20) Benzyl alcohol (C7H8O) oil of [37] abortifacient and anti-endometriosis activities [6- flower Essential 12]. Phytochemical investigations have reported (21) Salicylic acid (C7H6O3) oil of [37] some cardiac glycosides from wallflower organs flower Glucosinolates and isothiocyanates and concomitantly safety concerns of medicinal Essential application of the herb fell into a doubt [17,22]. oil of Probably it became the reason that wallflower is flower, (22) Cheiroline (C H NO S ) [4,19,40] 5 9 2 3 seed, leaf, not popular in current medicine. Nowadays, there fruit, are some traditional medicine preparations flower (23) Glucocheirolin (C11H21NO11S3) Seed [41] around the world, still applying wallflower as an (24) Iberin (C5H9NOS2) Seed [4] ingredient [28,32]. Recently, topical dosage (25) Glucoiberin (C11H21NO10S3) Seed [4] forms of wallflower has been suggested for (26) Ibervirin Seed [13] Miscellaneous nitrogen containing groups clinical skin diseases [26]. According to new in (27) Choline (C5H14NO) Seed [15] vitro/ in vivo pharmacological studies, cardiac Essential (28) Anthranilic acid (C7H7NO2) oil of [39] steroids in low doses (below their IC50) have flower shown stimulatory effects on Na+/K+ ATPase Aliphatics Essential pumps that occurs in safe dose below their (29) Acetic acid (CH3COOH) oil of [37] minimum toxic concentrations [52-54]. Therefore, flower dose adjustment of wallflower products are (30) Palmitic acid (C16H32O2) Seed [39] (31) Lignoceric acid (C24H48O2) Seed [39] necessary in order to decrease side effects of (32) Linolenic acid (C18H30O2) Seed [39] probable cardenolide constituents. It is suggested

88 Res J Pharmacogn 6(2): 85-95 Erysimum cheiri that IC50 value of cardenolide extract from the digoxin) as an indicator. On the other hand, whole product could be a good criteria to cardenolide's amount fraction could be estimated evaluate safety of wallflower preparations. For according to HPTLC-densitometry calibration this purpose, IC50 value of an extract of curve to a standard cardiac steroid (e.g. digoxin). wallflower product could be compared with IC50 This method may provide information about value of a known cardiac steroid (for example safety degree of wallflower traditional products.

Terpenoides  Cardiac steroids

Group of "Strophanthidin" O O

OHC H

HO OH (1) 3-O-[β-D-Glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranoside]

(2) 3-O-(6-Deoxy-β-D-glucopyranoside)

(3) 3-O-[β-D-Glucopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranoside]

(4)3-O-[β-D-Glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranoside]

Group of "Bipindogenin" O

HO OH (5) 3-O-(6-Deoxy-α-L-glucopyranoside)

(6) 3-O-[3-O-Methyl-β-D-glucopyranosyl-(1→4)-6-deoxy-α-L-glucopyranoside]

(7) 3-O-[β-D-Rhamnopyranosyl-(1→4)-β-D-glucopyranoside]

Figure 1. Chemical structure of natural compounds in wallflower (see table 1)

89 Mosleh G. et al.

Group of "Uzarigenin" O O

HO H (8) 3-O-[β-D-Glucopyranosyl-(1→4)-β-D-fucopyranoside]

(9) 3-O-[β-D-Glucopyranosyl-(1→4)-β-D-glucopyranoside]

Group of "Cannogenol" O O

H HOH2C

HO H (10) 3-O-[β-D-Glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranoside]

Group of "Digitoxygenin" O O

HO H (11) 3-O-[β-D-Glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-fucopyranoside]

Monoterpenoids

HO 3,7-Dimethyl-2,6-octadien-1-ol (C10H18O)

(12) (E) form: Geraniol (13) (Z) form: Nerol

Figure 1. Continued

90 Res J Pharmacogn 6(2): 85-95 Erysimum cheiri

(14) (R) form: Linalool

Flavonoids OMe

O OH HO

OH OH O

(15) Isorhamnetin (C16H12O7) (16) Isorhamnetin: 3-O-α-L-Arabinopyranoside, 7-O-α-L-rhamnopyranoside

O HO

OH OH O (17) Kaempferol (C15H10O6)

Cyanidins OH OH

O+ HO

OH OH (18) (E) derivative: 3-O-[β-D-Xylopyranosyl-(1→2)-[4-hydroxy-E-cinnamoyl-(→6)]-β-D-glucopyranoside], 5-O-β-D-glucopyranoside (Z) derivative: 3-O-[β-D-Xylopyranosyl-(1→2)-[4-hydroxy-Z-cinnamoyl-(→6)]-β-D-glucopyranoside], 5-O-β-D-glucopyranoside

Minor phenylpropanoids:

HOC COOH

OH OH

OCH3 (19) Anis aldehyde (C8H8O2) (20) Benzyl alcohol (C7H8O) (21) Salicylic acid (C7H6O3)

Glucosinolates and isothiocyanates

(22)Cheiroline(C5H9NO2S3) (24)Iberin (C5H9NOS2)

(25)Glucoiberin(C11H21NO10S3) (23) GlucocheirolinC11H21NO11S3) Figure 1. Continued

91 Mosleh G. et al.

(26) Ibervirin (C5H9NS2)

Miscellaneous nitrogen-containing structures COOH

OH NH2

(27) (28) Anthranilic acid (C7H7NO2) Aliphatics

O O

OH (30) OH (29)

HO O O OH

(32)

(33)

(31)

Figure 1. Continued Acknowledgments Declaration of interest This study was supported by a grant (95-01-05- The authors declare that there is no conflict of 11993) from Shiraz University of Medical interest. The authors alone are responsible for the Sciences. This study was part of the Ph.D thesis content of the paper. of Ghazaleh Mosleh. The authors would like to thank the vice chancellor of research and the References research and consultation center in Shiraz [1] The plant list. Erysimum × cheiri (L.) Crantz. University of Medical Sciences for their [Accessed 2018]. Available from: contributions to this study and editing the http://www.theplantlist.org/tpl1.1/record/kew manuscript. -2799915. [2] Missouri Botanical Garden, St. Louis, MO & Author contributions Harvard University Herbaria, Cambridge, Ghazaleh Mosleh contributed as Ph.D. MA.Cheiranthuscheiri Linn. flora of student and the main study investigator; Pakistan. [Accessed 2018]. Available from: Amir Azadi, Parmis Badr, Zohreh http://www.efloras.org/florataxon.aspx?flora Abolhassanzadeh, Seyed Vahid Hosseini and _id=5&taxon_id=200009360. Abdolali Mohagheghzadeh contributed as [3] Erum A, Aslam M, Jafri MA, Ahmed MA, supervisors of the whole project. All authors Yousuf AW. Phytochemical and approved the final draft of the manuscript. ethnopharmacological review of “Tudri

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Cranz) administration in anal fissure. Res J Abbreviations Pharmacogn. In press. PM: Persian medicine; IC50: Inhibitory concentration 50